{"author":[{"last_name":"Sieland","full_name":"Sieland, Benedikt","first_name":"Benedikt"},{"last_name":"Hoppe","full_name":"Hoppe, Axel","id":"62844","first_name":"Axel"},{"first_name":"Arne J.","full_name":"Stepen, Arne J.","last_name":"Stepen"},{"orcid":"0000-0002-3698-668X","last_name":"Paradies","full_name":"Paradies, Jan","first_name":"Jan","id":"53339"}],"year":"2022","main_file_link":[{"open_access":"1","url":"https://advanced.onlinelibrary.wiley.com/doi/10.1002/adsc.202200525"}],"user_id":"62844","_id":"59619","language":[{"iso":"eng"}],"title":"Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis","publisher":"Wiley","volume":364,"keyword":["hydroboration","nitrile","amine","frustrated Lewis pair","density functional theory"],"type":"journal_article","page":"3143-3148","date_updated":"2025-04-22T06:12:05Z","doi":"10.1002/adsc.202200525","quality_controlled":"1","date_created":"2025-04-22T06:01:56Z","status":"public","abstract":[{"lang":"eng","text":"<jats:title>Abstract</jats:title><jats:p>A frustrated Lewis pair‐catalyzed hydroboration of aromatic and aliphatic nitriles was developed. The catalyst provides the primary amines in high yields of 77–99% with catalyst loading as low as 2 mol%. The reaction displays high functional group tolerance towards esters, amides, nitro groups and aliphatic halides. The addition of the diborylated amines to ethyl 3‐phenylpropiolate proceeds with Z‐selectivity with d.r. of &gt;99:1 in 77–90% yield over two steps. The reaction mechanism was investigated by control and computational experiments.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\" mimetype=\"image/png\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic/adsc202200525-toc-0001-m.png\"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text>\r\n</jats:p>"}],"publication_identifier":{"issn":["1615-4150","1615-4169"]},"department":[{"_id":"389"}],"publication_status":"published","issue":"18","citation":{"ieee":"B. Sieland, A. Hoppe, A. J. Stepen, and J. Paradies, “Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis,” <i>Advanced Synthesis &#38;amp; Catalysis</i>, vol. 364, no. 18, pp. 3143–3148, 2022, doi: <a href=\"https://doi.org/10.1002/adsc.202200525\">10.1002/adsc.202200525</a>.","short":"B. Sieland, A. Hoppe, A.J. Stepen, J. Paradies, Advanced Synthesis &#38;amp; Catalysis 364 (2022) 3143–3148.","apa":"Sieland, B., Hoppe, A., Stepen, A. J., &#38; Paradies, J. (2022). Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis. <i>Advanced Synthesis &#38;amp; Catalysis</i>, <i>364</i>(18), 3143–3148. <a href=\"https://doi.org/10.1002/adsc.202200525\">https://doi.org/10.1002/adsc.202200525</a>","chicago":"Sieland, Benedikt, Axel Hoppe, Arne J. Stepen, and Jan Paradies. “Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis.” <i>Advanced Synthesis &#38;amp; Catalysis</i> 364, no. 18 (2022): 3143–48. <a href=\"https://doi.org/10.1002/adsc.202200525\">https://doi.org/10.1002/adsc.202200525</a>.","bibtex":"@article{Sieland_Hoppe_Stepen_Paradies_2022, title={Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis}, volume={364}, DOI={<a href=\"https://doi.org/10.1002/adsc.202200525\">10.1002/adsc.202200525</a>}, number={18}, journal={Advanced Synthesis &#38;amp; Catalysis}, publisher={Wiley}, author={Sieland, Benedikt and Hoppe, Axel and Stepen, Arne J. and Paradies, Jan}, year={2022}, pages={3143–3148} }","mla":"Sieland, Benedikt, et al. “Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis.” <i>Advanced Synthesis &#38;amp; Catalysis</i>, vol. 364, no. 18, Wiley, 2022, pp. 3143–48, doi:<a href=\"https://doi.org/10.1002/adsc.202200525\">10.1002/adsc.202200525</a>.","ama":"Sieland B, Hoppe A, Stepen AJ, Paradies J. Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis. <i>Advanced Synthesis &#38;amp; Catalysis</i>. 2022;364(18):3143-3148. doi:<a href=\"https://doi.org/10.1002/adsc.202200525\">10.1002/adsc.202200525</a>"},"publication":"Advanced Synthesis &amp; Catalysis","oa":"1","intvolume":"       364"}